MICHAEL ADDITION OF ACYCLIC LITHIUM 1,3-DIEN-2-OLATES WITH ALPHA,BETA-UNSATURATED ESTERS, KETONES, AND DIESTERS

被引：14

作者：

KANEMASA, S ^{[1
]}

KUMEGAWA, M ^{[1
]}

WADA, E ^{[1
]}

NOMURA, M ^{[1
]}

机构：

[1] KYUSHU UNIV, INTERDISCIPLINARY GRAD SCH ENGN SCI, DEPT MOLEC SCI & TECHNOL, KASUGA, FUKUOKA 816, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1991年 / 64卷 / 10期

关键词：

D O I：

10.1246/bcsj.64.2990

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Michael addition of lithium 1,3-dien-2-olates with alpha,beta-unsaturated carbonyl compounds is described. With alpha,beta-unsaturated esters the reaction was reversible even at -78-degrees-C, while kinetically controlled with alpha,beta-unsaturated ketones or alkylidenemalonates. At room temperature, the initially formed Michael adducts undergo subsequent intramolecular Michael addition to give substituted cyclohexanone derivatives in a highly stereoselective manner. Mostly anti-selectivity has been observed for the initial Michael addition, and the intramolecular cyclization was cis-selective.

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页码：2990 / 3004

页数：15

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